European Patent Applications 203,618 and 293,943 describe 1-benzoyl-3-aryl-urea derivatives having insecticide activity. Various substituted phenols are reacted with trifluorovinyl ethers under basic conditions (i.e., metal salts of the phenols). One group on the trifluorovinyl ether oxygen is (cyclo)alkyl or (cyclo)alkenyl, any of these optionally substituted with halogen. In a typical reaction, in 203,618, 2,6-dichloro-4-aminophenol reacts with perfluoro(ethyl vinyl ether) catalyzed by either sodium or sodium hydride in dioxane solvent, giving 3,5-dichloro-4-[2-(perfluoroethoxy)-1,1,2-trifluoroethoxy]aniline. However, the references do not disclose, groups in the trifluorovinyl ether other than (cyclo)alkyl or (cyclo)alkenyl in contrast to the ester group useful in the present invention.
Alcohols are also known to add to fluorinated vinyl ethers, see for example European Patent Application 254,632 and J. Org. Chem., vol. 49, pp. 7 4007-4008 (1984).
U.S. Pat. No. 4,281,092 reports the reaction of ammonia with a fluorinated vinyl ether ester. Instead of adding to the vinyl group, the ammonia adds to the ester group.
It is an object of the present invention to provide aryloxyfluoroether esters, acids and alcohols that are useful as intermediates in the preparation of monomers for polymerization. The present aryloxyfluorovinylether esters can be reduced by conventional means to form alcohols. These and other objects, features and advantages will become readily apparent upon having reference to the following description of the invention.